Diisopropylethylamine → [1,2,4]Triazolo[1,5-a]pyrimidin-2-amine, 5,7-dimethoxy-

HRID 479293Notes

Reaction equation

HRID 479293 reaction equation
C(=NC(=O)O[NH:6][C:7]1[N:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([O:15][CH3:16])[N:8]=1)=S.Cl.[NH2:19]O.C([N:24]([CH:27](C)C)CC)(C)C>C(O)C>[NH2:19][C:27]1[N:6]=[C:7]2[N:8]=[C:9]([O:15][CH3:16])[CH:10]=[C:11]([O:13][CH3:14])[N:12]2[N:24]=1

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 443297Hydroxyamine hydrochlorideHCID 86758830(4,6-Dimethoxypyrimidin-2-yl)amino carbonothioylcarbamate

Product 1

HCID 11194901[1,2,4]Triazolo[1,5-a]pyrimidin-2-amine, 5,7-dimethoxy-Yield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl [(4,6-dimethoxypyrimidin-2-yl)amino carbonothioylcarbamate (0.50 g, 1.7 mmol) was mixed with ethanol (5 mL). To this mixture was added hydroxylamine hydrochloride (0.12 g, 1.7 mmol) and diisopropylethyl-amine (0.30 mL, 1.7 mmol). The resulting mixture was allowed to stir at room temperature. After 2.5 hours, additional diisopropylethylamine (0.30 mL, 1.7 mmol) was added to the mixture. After 48 hours the ethanol was removed in vacuo and the residue was partitioned between H2O and Et2O to give a powder. The powder was filtered and dried to afford the product as a tan powder (0.27 g, 82%). mp 215-220° C. Anal: Cacld for C7H9N5O2: C, 43.08; H, 4.65; N, 35.88; O, 16.39; found: C, 39.88; H, 4.22; N, 32.00; O, 16.35. 1H NMR (DMSO-d6): δ 6.04 (s, 1H); 5.97 (br, 2H); 4.04 (s, 3H).

Workup

  1. customAfter 48 hours the ethanol was removed in vacuo
  2. customthe residue was partitioned between H2O and Et2O
  3. customto give a powder
  4. filtrationThe powder was filtered
  5. customdried

Sources & evidence

ORD record
ord-a28c8d32c77742ac9c3cf875310ced93
Source dataset
uspto-grants-2003_11
Patent number
US06645918B1

Reaction notes

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